Kekulene

Kekulene

Names
Other names [12]–Coronaphen, [12]Circulene
Identifiers
CAS Number	15123-47-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:32987 N
ChemSpider	4574217 N
PubChem CID	5460755
CompTox Dashboard (EPA)	DTXSID10420119
InChI InChI=1S/C48H24/c1-2-26-14-28-5-6-30-16-32-9-10-34-18-36-12-11-35-17-33-8-7-31-15-29-4-3-27-13-25(1)37-19-39(27)41(29)21-43(31)45(33)23-47(35)48(36)24-46(34)44(32)22-42(30)40(28)20-38(26)37/h1-24H N Key: TYPKKLUFDMGLAC-UHFFFAOYSA-N N InChI=1/C48H24/c1-2-26-14-28-5-6-30-16-32-9-10-34-18-36-12-11-35-17-33-8-7-31-15-29-4-3-27-13-25(1)37-19-39(27)41(29)21-43(31)45(33)23-47(35)48(36)24-46(34)44(32)22-42(30)40(28)20-38(26)37/h1-24H Key: TYPKKLUFDMGLAC-UHFFFAOYAP
SMILES C1=CC2=CC3=C4C=C2C5=CC6=C(C=CC7=CC8=C(C=C76)C9=CC2=C(C=CC6=C2C=C2C(=C6)C=CC6=C2C=C4C(=C6)C=C3)C=C9C=C8)C=C51
Properties
Chemical formula	C48H24
Molar mass	600.720 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Kekulene is a polycyclic aromatic hydrocarbon and a circulene with the chemical formula C₄₈H₂₄. It was first synthesized in 1978, and was named in honor of August Kekulé, the discoverer of the structure of the benzene molecule.

References

• Peter, R.; Jenny, W. (1966). "250. Höhere, kondensierte Ringsysteme. 1. Mitteilung [1]: Untersuchungen in der [10]-Coronaphenreihe: Synthese von Di-[benzo(c)phenanthren-3, 10-dimethylen]". Helvetica Chimica Acta. 49 (7): 2123. doi:10.1002/hlca.660490717.
• Staab, Heinz A.; Diederich, François (1983). "Cycloarenes, a New Class of Aromatic Compounds, I. Synthesis of Kekulene". Chemische Berichte. 116 (10): 3487. doi:10.1002/cber.19831161021.
• Krieger, Claus; Diederich, Francois; Schweitzer, Dieter; Staab, Heinz A. (1979). "Molecular Structure and Spectroscopic Properties of Kekulene". Angewandte Chemie International Edition in English. 18 (9): 699. doi:10.1002/anie.197906991.
• Aihara, Junichi (1992). "Is superaromaticity a fact or an artifact? The kekulene problem". Journal of the American Chemical Society. 114 (3): 865. doi:10.1021/ja00029a009.
• Diederich, François; Staab, Heinz A. (1978). "Benzenoidversus Annulenoid Aromaticity: Synthesis and Properties of Kekulene". Angewandte Chemie International Edition in English. 17 (5): 372. doi:10.1002/anie.197803721.
• Jiao, Haijun; Schleyer, Paul von Ragué (1996). "Is Kekulene Really Superaromatic?". Angewandte Chemie International Edition in English. 35 (20): 2383. doi:10.1002/anie.199623831.
• Schweitzer, D.; Hausser, K.H.; Vogler, H.; Diederich, F.; Staab, H.A. (1982). "Electronic properties of kekulene". Molecular Physics. 46 (5): 1141. doi:10.1080/00268978200101861.
• Cioslowski, Jerzy; O'Connor, Peter B.; Fleischmann, Eugene D. (1991). "Is superbenzene superaromatic?". Journal of the American Chemical Society. 113 (4): 1086. doi:10.1021/ja00004a005.
• Staab, Heinz A.; Diederich, FrançOis; Krieger, Claus; Schweitzer, Dieter (1983). "Cycloarenes, a New Class of Aromatic Compounds, II. Molecular Structure and Spectroscopic Properties of Kekulene". Chemische Berichte. 116 (10): 3504. doi:10.1002/cber.19831161022.
• Zhou, Zhongxiang (1995). "Are kekulene, coronene, and corannulene tetraanion superaromatic? Theoretical examination using hardness indices". Journal of Physical Organic Chemistry. 8 (2): 103. doi:10.1002/poc.610080209.